


Jessie's Sex Adventures

by TheGreenArrowDP2001



Category: Disney - All Media Types, Jessie (TV)
Genre: Anal Sex, F/M, Multi, Oral Sex, Rough Sex, Sex, Vaginal Sex
Language: English
Status: In-Progress
Published: 2018-11-11
Updated: 2018-11-10
Packaged: 2019-08-21 22:28:24
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,650
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16585454
Author URL: https://archiveofourown.org/users/TheGreenArrowDP2001/pseuds/TheGreenArrowDP2001
Summary: Characters from Jessie have sex.





	1. Chapter 1: Ravi and Jessie

Ravi was sitting in his room doing his homework when he heard noises coming from outside. He was 16, and had grown taller from him middle school size. He also didn't have his bowl cut, and now had short hair.

He was curious as to what was distracting him from his work, and he opened his door and peeked around, and the source of the noises became obvious; it was coming from Jessie's room.

Emma was out with some friends for a sleepover and Luke was also at a sleepover. When he had learned of this, he bragged about a Mathletes Party he was invited to and that he was going, but there was no party. Zuri and Bertram were asleep and both of them were nearly impossible to wake up so it was him, Zuri, Bertram and Jessie in the penthouse.

He slowly walked toward Jessie's room, and the noises were more clearer. It sounded like moans, and Ravi could hear Jessie saying muffled things; "Oh my god! god! god! god!", "Yes yes yes yes yes yes." and "I'm gonna cuumm!".

He turned the knob on the door and he opened it slightly and peeked through and what he saw froze him. It was Jessie, on her bed, with her shirt on the floor, and one hand through her skirt, and Ravi could see the hand was spasming between her legs. Her other hand was massaging her breasts, pinching her nipples.

Ravi stood there peeking, and he felt his pants tighten. He stared down and he saw his pants were sticking out in a tent formation.

When his dick became erect for the first time after seeing Emma in a two piece bikini; he had learned all there is to know about the penis as well as women parts. After all, he looked up things to learn.

His penis was normally 4 inches when he was flaccid (not erect), but when he had become erect, he measured to be 6 inches. He had only become erect twice, first from Emma, and now from Jessie.

He then remembered the steps to relieve an erection, which he hadn't attempted before but he was going attempt it when Emma had given him an erection, but by the time he had learned everything, he became flaccid.

Ravi unzipped his pants and he let them fall, as well as his dinosaur underwear. His dick was sticking straight out.

Jessie was to much into playing with herself to notice Ravi peeking in the room. Ravi started to feel his testicles swell and he groaned as he had never experienced this before.

His groan had caught Jessie's attention and she stopped and looked around.

"Who's there?" She asked, and Ravi made a move to hide but tripped because his pants were around his legs. She spotted Ravi falling and ran to the door, swinging it open.

"Ravi! What are you doing?" She said to the boy on the floor, nearly yelling but not loud enough to wake Zuri up.

"Oh nothing. Absolutely nothing at all." Ravi said.

"Wait, were you watching me playing with myself?" She said.

"I heard noises and I thought Ms. Kipling had gotten into your room again. So I came and then I saw you playing with yourself." He replied as he stood up, pulled his pants back up and faced Jessie. It was obvious that he had a bulge in his pants.

"Did…Did you like it?" Jessie asked as she saw Ravi's bulge.

"Umm... Yes I guess I did." Ravi said.

Ravi stared at her gorgeous body and her tits, captivated by her beauty.

"Do you want some help with that?" She said still staring at his bulge.

"YES!" Ravi blurted out maybe too loud.

Jessie led Ravi to her bed and she pushed him back on the bed gently. She then unbuttoned and removed his pants and underwear. Ravi was losing his erection, and he was disappointed.

"Oh, I know what we can do to get you back to being that big." She said as she leaned on Ravi and they started making out.

Jessie's hand started exploring Ravi's body. Their tongues clashed against each other. Jessie took off Ravi's shirt, revealing his six-pack. She kissed his chest and her fingers explored his abs. Ravi groaned as his penis grew to 6 inches again.

Jessie stopped kissing Ravi when she felt the head of his dick rub against her smooth stomach. She grabbed it and rubbed it around.

Jessie got off of Ravi and onto her knees smiled at Ravi. She leaned forward and kissed the tip slowly. Her soft and luscious lips wrapped tightly around Ravi's sensitive head, and her tongue shot out and teased the head.

Her lips made a 'Pop' noise when Jessie's lips slipped the head out. He knew all about teasing, as well as the act of Fellatio (blowjobs). Ravi then moved his hand and forced her head towards his dick again.

She opened her mouth and shoved it in. He pushed her head down until he was rubbing the back of her throat and the pretty Texas girl began to slobber on his dick. He released her head and Jessie pulled back and she took deep breaths until she caught it.

"Damn, that brings me back to junior high. It's a shame that Tony isn't that big." She said, as she began to jerk off Ravi's saliva-covered dick. Ravi felt the same feeling of his testicles swelling and Jessie could feel the large cock pulse in her hands.

"Looks like someone's close to blowing their first load." Jessie said as she moved between Ravi's legs.

She then positioned the head of Ravi's dick to her face and began to jerk him off with both hands.

"Lets blowing it in my mouth and all over my face and titties, how bout that?" she said as she kissed the head again and sped up her hands.

"Ungggh Jessie. I'm gonna... Yes. Yes. Here it comes!" Ravi moaned as he blew his load all over his babysitter's face and tits and her stomach and in her stomach. Thick long ropes shot out of Ravi's dick and went into Jessie's waiting mouth, and when her mouth was filled she moved back and the warm ropes of cum splattered onto her.

"Oh wow that was a lot. I guess that's what happens when you don't cum for 2 years." Ravi said as he looked at Jessie. She closed her eyes and smiled as Ravi's jizz traveled down her throat.

"Damn, it's spicy." She said as it traveled through the rest of her body. She cleaned Ravi's tip, and then began to clean the jizz off of her. She dragged fingers along her body and would drip it into her mouth.

When Jessie thought that she had cleaned everything up, she leaned onto Ravi again and began making out with him again (she has some on her throat.)

Jessie's phone began to buzz and she saw it was Luke calling.

She answered the call and she and Luke talked for a few minutes, meanwhile Jessie was rubbing Ravi's cock. She ended the call and said that Luke's friends made fun of Kenny the Koala and that he needed a ride home so she had to get him.

"I'm sorry to go and leave you like this Ravi. Maybe we can finish all this properly another time." She said as she began reclothing herself. She gave Ravi a kiss before she left.

"Well that was fun." Ravi said as he got up and pulled his pants back up and walked to his room. He sat down and then removed his pants and started to jerk off.

He then heard Ms. Kipling groans that meant she had just pooped.

"Great." he said as he grabbed the special bags to dispose of the reptilian waste.

He cleaned it up and disposed of it properly before he got an idea.

I grabbed another bag and he resumed jerking off. He kept going until he blew a load into the bag. Then he crept into Jessie's room and he placed it under her pillow, and then left. She was gonna have a present until they finished what they started.


	2. Chapter 2: Ravi and Jessie

**Summary for the Chapter:**

> Ravi and Jessie finish what they started the previous night and the plot thickens when someone finds out about them.

Jessie had just picked up Luke from his sleepover. As she drove to pick him up, she was remembering the blowjob she had given Ravi and the spicy taste of his jizz as it went down her throat. When Luke got in the car, he didn't talk.

He looked at Jessie and then he pointed on her neck. "Hey, what's that on your neck?" Luke asked curiously.

He was pointing at Ravi's cum which she hadn't noticed was still on there.

"Oh, its food. I was eating a sandwich and the mayo bottle exploded." She said fast.

She collected Ravi's cum and swallowed the last bit, and the spiciness got her.

"Mmm, mayo is good." she said to convince Luke.

"Jessie, you're weird." Luke replied

"Says the high-school student that still sleeps with a stuffed koala bear." Jessie snapped back.

"Hey, Kenny is a limited time stuffed animal." Luke said, (I don't know if he is or not.)

"Whatever you say weirdo." Jessie said.

They didn't say anything until they got the penthouse, and Luke went to his room. Jessie walked upstairs and she stood at the door. She turned to go knock on Ravi's door when Luke came out and went downstairs without noticing her.

Jessie decided to just go to sleep and talk to Ravi tomorrow. She changed into her pj's and she got into bed. Her hand moved under her pillow and she felt something. She pulled it out and turned the lamp next to her bed on.

It was a baggie full of something white and creamy. The baggie was warm and when she opened the bag and smelled it, she instantly knew what it was.

"Thanks for the present Ravi." She said as she sat up, closed the bag and went down to the kitchen for a straw. She ran up to her room and closed the door, turned on the TV and she laid down and starting drinking.

"Mmmm. Who knew Bertram's food could make jizz taste good." She said to herself when she finished the cum.

She then brushed her teeth, set her alarm for tomorrow morning and went to bed.

THE NEXT MORNING

Jessie woke up at 7am, and she brushed her teeth and took a shower. It was Sunday so everyone would sleep in, except for Ravi. Jessie knew that if they both wanted to finish what they were doing yesterday, they would have to do it early.

Jessie was wearing short jean shorts, and a small shirt that was tight. She walked to Ravi's room and knocked on the door. When she walked in she saw Ravi was sitting his chair watching TV.

Ravi got up and greeted Jessie and she walked up to him and kissed Ravi.

Wow, Jessie! You look very sexy." Ravi said.

He returned the kiss, and his hands grabbed her ass tightly.

"Awww, thanks!" Jessie said.

"Oh my, someone's excited." She said as she could feel Ravi's erection rising against her thigh.

"Why don't we give him some air." She said as she took a step back.

Ravi pulled off his pants and underwear and his rock hard 6 inch dick sprung out.

Ravi pushed Jessie on her back on the bed and said that he wanted to continue exactly where they left off.

"Funny, I was going to say the exact same thing." Jessie said as Ravi got on top of her and started to slowly slide into her with his dick.

She groaned as Ravi's kebob stretched her pussy out. Jessie had an orgasm right there and her juices lubed Ravi's dick up.

"Now move in and out, in and out at a nice steady speed." Jessie said to Ravi.

Ravi began to slowly fuck Jessie and it was obvious that he was getting her good, judging from the moans.

He began to pick up the pace and Jessie had no objections to that. His hands started to explore Jessie's curves and her tits.

"Ravi yes, oh my god! Ravi...yes!" Jessie moaned as Ravi pushed deeper and harder into her wet pussy.

Ravi was fucking Jessie in a wild style, making her big sexy boobs bounce each time he thrusted into her.

He then grabbed her hips and he started to pull her down and up. He surprised Jessie by his strength, as he was still a little skinny, but was strong enough to move her. He was thrusting along with Jessie's hip movements.

"Ravi, don't stop! Keep banging my awesome pussy like that!" Jessie moaned.

"Aaaahhhh, oooohhhhh! YES!" moaned Jessie as she got another orgasm.

"Jessie! Oh yeah! Holy shit, yes!" Ravi moaned as he came hard into Jessie's pussy unexpectedly.

Jessie pulled off of Ravi's dick and rolled over.

Jessie caught her breath and rolled onto Ravi. She kissed him while Ravi grabbed her tits and squeezed them, which made Jessie moan loudly.

"I'm all yours." Jessie said as she got on her knees so Ravi could go behind her, then Jessie got on her hands and knees.

Ravi moved around and his dick rubbed Jessie's asshole. He pushed in without warning and they both moaned loudly. Jessie hadn't felt anything like this in her ass in a long time! He thrusted hard into her again and again.

Jessie moaned in pleasure as she had an orgasm so hard, that her body vibrated. Ravi pulled out his cock and aimed it at the entrance of Jessie's tight asshole.

Ravi then moved one hand to her clitoris while the other grabbed a nipple hard. He started to play with her clit fast making her wet and have another orgasm. The orgasm arched her back and her head went back so that Ravi was able to kiss her.

Ravi got on his knees and he kissed her, his dick sliding between her ass cheeks, and her naked back rubbed against his chest. Ravi then rammed hard all the way into Jessie's tight asshole and she let out a loud scream. Ravi kissed Jessie to silence her.

Ravi was now fucking the shit out of Jessie so hard that she was screaming from the intense pleasure. She then squirted all over Ravi's bed and his thigh. Ravi pulled out of Jessie's asshole and told her he was about to cum.

She turned around and got on her back. Ravi stood at the end of the bed, and he started to jerk off. Jessie lifted her head and started suckling on Ravi's balls.

Ravi groaned and his balls clenched hard, and he released his load onto Jessie's face and body and into her mouth. Ropes after ropes of warm, spicy, white jizz spewed out on the pretty Texas nanny.

Jessie spent the next 10 minutes cleaning the jizz off of her. They were both sweaty and they kissed for a little before they took showers in their own rooms.

When they were done, everyone else had woken up and were eating breakfast. Jessie came down and sat across from Ravi, and her foot started to rub his dick.

They all finished and Jessie told them to finish their homework, and not to come out until they were done. Jessie told Luke to give her his phone and he wouldn't get it back until he was done all the way.

End of Chapter 2... Next Chapter is gonna have a little Jessie/Ravi with the starting of Jessie/Luke.


	3. Chapter 3: Luke Watches A Hot Video

**Summary for the Chapter:**

> Luke finds the video Ravi made with Jessie and is alone.

When they all finished breakfast, the kids went to do their homework. She took Luke's phone and put it in her pocket, and told him he could have when he finished. Ravi, being the kid that he is, had already finished his homework, and was relaxing, playing on his phone. Jessie knew this, so she decided to visit Ravi. She locked the door when she went to his room and she jumped on him, Ravi's phone was knocked out of his hand and fell off the bed.

They started to kiss, and Jessie was rubbing her crotch against Ravi's growing bulge. Ravi moved to the edge of the bed and Jessie sat on his lap and they started to dry hump.

Jessie sat up and threw her pants off and Luke's phone fell out. Her pants fell on Ravi's phone as Jessie started kissing Ravi. Luke's phone and Ravi's phone had the same cases, because they got the phones for Christmas. Jessie got on her knees and she kissed Ravi's bulge.

She undid the button on his jeans and pulled them down. Ravi's dick was thriving for freedom from his boxers and Jessie gently kissed the bulge. She licked up and down, and her hand started to grab the balls outside the boxers.

She pulled down the top of Ravi's boxers, exposing his head, which was suffocated by Jessie's plump lips. She squeezed her lips tightly, and her tongue jetted out to greet the head. Her tongue swirled around, and Jessie slowly pulled down the boxers, exposing more and more of Ravi's dick. Jessie's mouth took in more of Ravi's cock as it was freed from the boxers. She pulled down the boxers all the way and she pulled back.

She told Ravi to grab his phone and he got up and looked around for it. He spotted Luke's phone and picked it up thinking it was his, and he sat back down on the bed.

"I want you to record your nanny sucking your dick until you blow your spicy cum in my mouth." Jessie said as she took a testicle into her mouth, suckling on it.

"You got it Jessie, let me know when you're ready." Ravi replied.

"Start in 3. 2. 1." Jessie said as she plunged Ravi's dick in her mouth as she said 1. The dick rammed into her throat and it was all in her mouth, gagging her. She pulled back and she plunged again and again. She was playing with his balls at the same time as well.

Jessie started to jerk off Ravi's dick, the saliva all around it lubing it. She smiled sexily at the phone, and she then removed her T-shirt and bra and showed off her titties.

She then moved forward and she started to suffocate Ravi's dick between her beautiful titties. She started to bounce and gave Ravi his first titty-job. Ravi was having trouble keeping a steady hand, but he fought through it. Soon Jessie's tits had dried off the saliva on Ravi's dick, and Jessie started sucking on it again, and her saliva soaked the pulsing phallus in her mouth.

"Jessie I'm close to cumming." Ravi groaned.

"Yay, I can't wait for it." She said as she started jerking off Ravi's dick with two hands. Her hands worked in unison, one hand on top of the other, as they jerked up and down.

Jessie was talking about wanting his cum in her to the camera, and Ravi's free hand moved behind her hand and pushed her open mouth onto his dick. He pushed down as hard as he could and he wrapped a leg behind her head and held her there. His load blew out and the spicy jizz filled her mouth. His load was surprisingly big, as he did cum 3 times since yesterday and today. It was so big that Jessie couldn't keep it all in and it spilled out onto her tits and chest.

When Ravi was done blowing his load, Jessie opened her mouth to the phone and revealed the Indian boy's jizz swirling in her mouth. She closed her mouth, gulped, and reopened her mouth, showing an empty mouth. Ravi stopped the recording and took pictures of his jizz on his sexy nanny's body.

She finished the jizz and when she completely clean, they both started to get dressed. Ravi had to go to the bathroom and he threw Luke's phone onto Jessie's shirt. When she picked it up, she knocked it over and it fell to the floor next to her pants. She reached down and picked up the phone and her pants and she saw Ravi's phone under her pants.

"Huh, that's a little weird." Jessie said as she put Luke's phone into her pocket and put Ravi's phone on his bed. She waited until he came out to kiss him one more time, and to enjoy the video before she left to go to her room. She laid down and relaxed, and she drifted off to sleep.

She woke up to Luke pounding on her door, asking for his phone an hour later. She checked his homework and was surprised to see it was all done, and she gave him his phone.

Luke took his phone and he went to his room and he opened RichChat, the app for rich kids, it was like Snapchat but for rich people only. He took videos of himself bouncing on his trampoline bed, and he opened his camera roll to post them. When he was selecting them, he saw the picture of Jessie. He swiped and he found the other pictures and the video.

Luke got hard and his 6 inch dick stuck out after he took his pants off. He sat down in his chair and he started to jerk off to his nanny.

It took a few minutes to notice that Jessie was sucking on none other than Ravi's dick, and he jerked off to the thought of him being in Ravi's place. He was lost in his thoughts, and he didn't notice Emma walking in on him. She was angry that he had apparently put something in her hair conditioner. She had apparently just gotten out of the shower, as all she was wearing was a towel. She saw what Luke was doing, and she closed the door.


	4. Chapter 4: Emma and Luke

**Summary for the Chapter:**

> Emma busts Luke watching the video, then some fun happens but how far can they go without getting interrupted.

Emma walked towards Luke staring at his dick. It was so big and he was so much bigger than Xander. Emma only fucked him because she loved his abs.

But even then, his abs weren't enough to make up for his 3 inch dick. She thought all dicks were that size, that was until she saw her math teacher, Mr. Conodor's dick.

Mr. Conodor was nearly 5 inches and Emma remembered the day he fucked her. She had been failing and she stayed after school to see if there was something she could do. Instead he did her hard, and he came all over her face and in her hair.

She remembered how Jessie had spotted it in her hair, and how she almost got busted.

Emma heard moaning and she snapped back to the present. She kept walking up to Luke and she moved behind him and looked at what he was watching, she was stunned too.

She saw Jessie's mouth engulfing a dick that looked as big as Luke was. She stared at Jessie's face and she saw a hand move Jessie's hair out of her face, and she caught something on the wrist. It was a dinosaur watch, the same watch she gave Ravi.

"OMG! She's sucking Ravi's dick." She said. Luke still didn't notice her presence in the room. Emma watched as Luke continued to stroke his dick and Emma dropped her towel, leaned over and started jerking Luke's dick off.

Coincidentally, Jessie said in the video that she wanted to jerk you off. "You" being Ravi, and Luke stopped stroking himself and he tilted his head back and closed his eyes. Luke thought Jessie was jerking him off and he relaxed as 'Jessie' jerked him off.

Then Luke heard Ravi shouting he was close to cumming and he opened his eyes in confusion. In front of his face was Emma

"What the hell are you doing?" He said.

"Why were you watching this? And what the hell did you do to my hair?" She asked pissed. Her blonde hair had streaks of pink in them.

Emma's amazing tits hung over Luke's face; he zeroed in on them and completely forgot about everything else.

Emma realized Luke wasn't gonna answer her and she kept stroking Luke's cock.

Luke reached up with his hands and he grabbed Emma's tits and he started to nibble on one of her nipples.

Emma saw Luke's body and she was actually impressed. Luke had a six-pack and he did have some muscles. She sped up her stroking before she moved around to Luke's lap and she stared at his cock.

"You ever had a blowjob?" Emma asked.

"Pffft. Yeah... No." Luke said.

"Well I'm gonna give you one." Emma said as she move her amazing lips to the bulbous head of Luke's cock and engulfed it. She squeezed her lips together and then moved down and up.

She looked up at Luke and saw that his head was hanging back and he was groaning from the pleasure.

She then engulfed 2 more inches of Luke's cock, only leaving one inch out. She started bobbing and Luke's head snapped back and he watched Emma suck his dick.

Luke moaned and his hands moved to the back of Emma's head. He pushed down a little and Emma pulled her head back up.

"It's okay. You can push my head down. I want your whole dick in my mouth." Emma said." She said as she went down and continued sucking his dick.

Luke pushed her head down and he felt the back of his sister's cock. He held her down and he closed his eyes. Emma started gagging and Luke released her head and she gasped for air. She then plunged back down and she started deep-throating her adopted brother.

Luke stood up suddenly and Emma started to play with his balls. She pulled her head back and looked up at him.

"Fuck your sister's mouth." Emma said as she stuck her tongue out. Luke happily pushed his cock into her mouth. She gagged a little and Luke repeated the movement. He pulled all the way out and strands of saliva would hang from her mouth and his cock.

Emma stroked his cock and slathered the saliva onto the cock and Luke resumed fucking his gorgeous sister.

Luke then moaned as he felt himself getting close to cumming. She knew he was close when his dick started twitching in her mouth.

She pulled her head back and she started jerking Luke off fast.

"Cum for your big sister. Blow your load all over my face and my body. Cover my face with that hot cum." She said to him and Luke blew his load onto his sister's face. Emma jerked his cock until every drop of his load was out and on her face or tits.

Emma stood up and she smiled as she tasted some.

"Wow. Your jizz tastes pretty good." Emma said.

Suddenly, they both heard knocking on Luke's door and Jessie called him.

"Luke are you in there? Why's your door locked? We're going to see a movie, let's go." She said.

"Shit." Emma said as she grabbed her towel and wrapped it around her body and stood next to the door.

Luke shoved his cock back into his pants again and he opened the door.

"What movie are we watching?" Luke asked.

"Galactopus 2." Jessie said.

"Sweet." Luke replied as he walked out and closed the door.

Emma finished swallowing Luke's load off of her face and body and she ran to her room and she took another shower. She couldn't think of anything else except for Luke's cock. She needed it badly.

Next chapter will have sex, not revealing who will have it though. You'll have to read to find out. Don't forget to leave comments if you liked it.


End file.
